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Padalecki had an uncredited role as a high school bully in 2003's comedy Cheaper by the Dozen, which he played after being asked by fellow actor and friend Tom Welling, who played Charlie Baker, and the director of the movie, who wanted someone larger than Charlie to pick on him.Padalecki originally auditioned for Welling's role, but gave it up in order to film a pilot titled Young Mac Gyver which was never picked up.In 2000, he was cast as Dean Forester on the television series Gilmore Girls, a role he played until 2005.Throughout the early 2000s, he appeared in several made-for-television films, including Silent Witness, Close to Home, and the Disney Channel Original Movie A Ring of Endless Light.Padalecki proposed to in front of their favorite painting, "Joan of Arc", by French realist Jules Bastien-Lepage at New York's Metropolitan Museum of Art in October 2009.The pair married on February 27, 2010, in Cortese's hometown of Sun Valley, Idaho.

In 2005, he appeared in Cry Wolf, another horror film, as Tom.you’ve peed on me, pooped on me, and vomited on me (though not always necessarily in that order). you’ve coerced me into watching cartoons and animated movies over and over and over again… you’ve made me stop whatever I’m doing so that i can go catch the lizard you just spotted outside.you’ve yelled at me to stop the car to chase the deer or squirrels that you spotted.thank you for making me attempt warm-up-free wind-sprints midway into my thirties.thank you for making me remember why its so important to drive slowly through neighborhoods.

Padalecki's engagement to his Supernatural co-star Genevieve Cortese was announced in January 2010.